299964-35-5

Upstream product

• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 99-93-4 4-Hydroxyacetophenone 
• 100-44-7 benzyl chloride 

Downstream Products

• 188730-94-1 (R)-1-(4-benzyloxy-3-nitrophenyl)oxirane 
• 188730-96-3 (S)-4-benzyloxy-3-nitrostyrene oxide 
• 73573-87-2 (R,R)-formoterol 
• 299964-43-5 (R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 245759-61-9 (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 408497-91-6 N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 
• 1218777-34-4 5-(4-(benzyloxy)-3-nitrophenyl)oxazolidin-2-one 
• 1361398-74-4 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-75-5 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-76-6 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)pentyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-77-7 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)hexyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-78-8 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)ethyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-79-9 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-80-2 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)pentyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 

Relevant academic research and scientific papers

Design, synthesis and evaluation of dual pharmacology β2- adrenoceptor agonists and PDE4 inhibitors

A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high β2-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R,R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC50 = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 μM).

Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both b2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 μM, which was more potent than phthalazinone, IC50 = 0.520 lM) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC50 = 9.3).

An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

The potent β2-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. Copyright (C) 2000 Elsevier Science Ltd.

2-(3-Benzyloxy-4-nitrophenyl)oxirane, an Intermediate in the Synthesis of Formoterol

In the title compound, C15H13NO4, the two planar nitrophenyl and benzyloxy groups are inclined at 152.3(2) deg.The torsion angle about the central C-O bond is 177.5(5) deg, giving an extended C-C-O-C chain.The nitro group is twisted out of the plane of the phenyl ring by 28.4(3) deg to diminish steric hindrance; O atoms of the nitro and benzyloxy groups are separated by only 2.625(7) Angstroem.The dihedral angles between the epoxy ring and the two aromatic rings are 98.3(3) and 102.6(3) deg.There is a possible C-H...O intermolecular interaction.

Bronchospasmolytic phenylethanolamines

Phenylethanolamines of the formula I STR1 wherein R is substituted phenyl or optionally substituted furyl, thienyl, or pyridyl, R5 is hydrogen, lower alkyl, or optionally substituted benzyl, R4, R6, R8, and Rsu